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2012 Fiscal Year Final Research Report

Transformation of functional π-conjugated molecules into open-shell state

Research Project

  • PDF
Project/Area Number 22750036
Research Category

Grant-in-Aid for Young Scientists (B)

Allocation TypeSingle-year Grants
Research Field Organic chemistry
Research InstitutionNagoya University

Principal Investigator

HIROTO Satoru  名古屋大学, 工学研究科, 助教 (30547427)

Project Period (FY) 2010 – 2012
Keywordsラジカル / ポルフィリン / 多環芳香族炭化水素 / シクロファン
Research Abstract

We developed efficient method for introduction of various functionalities toward hexa-peri-hexabenzocoronenes. Second, we discovered that oxidation of amino-substituted porphyrins provided pyrazine-fused dimers in excellent yield with high regioselectivity. The pyrazine-fused dimers were also obtained by oxidation of amino-substituted anthracenes. In this case, pyrrole-fused dimer with helical conformation was obtained. Furthermore, oxidation of dihydroxyanthracenes afforded highly distorted [2.2]metacyclophanes.

  • Research Products

    (18 results)

All 2013 2012 2011 Other

All Journal Article (8 results) (of which Peer Reviewed: 8 results) Presentation (8 results) Book (1 results) Remarks (1 results)

  • [Journal Article] Functionalization of Hexa-peri-hexabenzocoronenes: Investigation of Substituent Effects on a Superbenzene2013

    • Author(s)
      R. Yamaguchi, S. Ito, B. S. Lee, S. Hiroto, D. Kim, H. Shinokubo
    • Journal Title

      Chem. Asian. J

      Volume: 8 Pages: 178-190

    • DOI

      DOI:10.1002/asia.201200723

    • Peer Reviewed
  • [Journal Article] Intermolecular Oxidative Annulation of 2-Aminoanthracenes to Diazaacenes and Aza[7]helicenes2012

    • Author(s)
      K. Goto, R. Yamaguchi, S. Hiroto, H. Ueno, T. Kawai, H. Shinokubo
    • Journal Title

      Angew. Chem. Int

      Volume: 51 Pages: 10333-10336

    • DOI

      DOI:10.1002/anie.201204863

    • Peer Reviewed
  • [Journal Article] Synthesis of Oxygen-Substituted Hexa-peri-hexabenzocoronenes through Ir-Catalyzed Direct Borylation2012

    • Author(s)
      R. Yamaguchi, S. Hiroto, H. Shinokubo
    • Journal Title

      Org. Lett

      Volume: 14 Pages: 2472-2475

    • DOI

      DOI:10.1021/ol300743f

    • Peer Reviewed
  • [Journal Article] Oxidative Annulation of β-Aminoporphyrins to Provide Pyrazine-Fused Diporphyrins2012

    • Author(s)
      M. Akita, S. Hiroto, H. Shinokubo
    • Journal Title

      Angew. Chem. Int

      Volume: 51 Pages: 2894-2897

    • DOI

      DOI:10.1002/anie.201108037

    • Peer Reviewed
  • [Journal Article] Synthesis and oxidation of cyclic tetraindole2012

    • Author(s)
      S. Nakamura, S. Hiroto, H. Shinokubo
    • Journal Title

      Chem. Sci.

      Volume: 3 Pages: 524-527

    • DOI

      DOI:10.1039/C1SC00665G

    • Peer Reviewed
  • [Journal Article] Functionalization of a Simple Dithienylethane via Palladium-Catalyzed Regioselective Direct Arylation2011

    • Author(s)
      H. Kamiya, S. Yanagisawa, S. Hiroto, K. Itami, H. Shinokubo
    • Journal Title

      Org. Lett

      Volume: 13 Pages: 6394

    • DOI

      DOI:10.1021/ol2026069

    • Peer Reviewed
  • [Journal Article] Iridium-Catalyzed Direct Tetraborylation of Perylene Bisimides2011

    • Author(s)
      T. Teraoka, S. Hiroto, H. Shinokubo
    • Journal Title

      Org. Lett

      Volume: 13 Pages: 2532

    • DOI

      DOI:10.1021/ol2004534

    • Peer Reviewed
  • [Journal Article] Synthetic protocol for diarylethenes through Suzuki-Miyaura coupling2011

    • Author(s)
      S. Hiroto, K. Suzuki, H. Kamiya, H. Shinokubo
    • Journal Title

      Chem. Commun

      Volume: 47 Pages: 7149-7151

    • DOI

      DOI:10.1039/C1CC12020D

    • Peer Reviewed
  • [Presentation] ヒドロキシオリゴアセンの酸化による二量化反応の研究2013

    • Author(s)
      廣戸 聡・小山 祐太朗・忍久保 洋
    • Organizer
      第93 日本化学会春季年会
    • Place of Presentation
      立命館大学 BKC(滋賀)
    • Year and Date
      2013-03-23
  • [Presentation] Masanari Akita, Hiroshi Shinokubo"Oxidative intermolecular dimerization of amino-substituted π-conjugated aromatic compounds2012

    • Author(s)
      Satoru Hiroto, Kiyohiko Goto
    • Organizer
      IKCOC-12
    • Place of Presentation
      リーガロイヤルホテル(京都)
    • Year and Date
      2012-11-15
  • [Presentation] Takeshi Kondo, Hiroshi Shinokubo"Synthesis of a Cyclic Tetraindole and Its Derivatives2012

    • Author(s)
      Satoru Hiroto, Shoichi Nakamura
    • Organizer
      ICPOC-21
    • Place of Presentation
      Durham University(UK)
    • Year and Date
      2012-09-12
  • [Presentation] π拡張[2.2]メタシクロファンの合成2012

    • Author(s)
      小山 祐太朗・廣戸 聡・忍久保 洋
    • Organizer
      次π空間の創発と機能開発第8回公開シンポジウム
    • Place of Presentation
      ホテルアローレ(石川)
    • Year and Date
      2012-07-19
  • [Presentation] Synthesis and Oxidative Annulation of β-aminoporphyrins2012

    • Author(s)
      Satoru Hiroto, Masanari Akita, Hiroshi Shinokubo
    • Organizer
      ICPP-7
    • Place of Presentation
      Jeju(韓国)
    • Year and Date
      2012-07-03
  • [Presentation] "遷移金属触媒によるジアリールエテンの修飾反応の開発", 科研費特定領域研究「フォトクロミズムの攻究とメカニカル機能の創出」2011

    • Author(s)
      廣戸聡、忍久保洋
    • Organizer
      第8回 最終公開シンポジウム
    • Place of Presentation
      東京大学(東京)
    • Year and Date
      2011-11-18
  • [Presentation] ペリレンビスイミドの直接ホウ素化を利用した窒素含有多環芳香族化合物の合成2011

    • Author(s)
      廣戸聡・伊藤覚・忍久保洋
    • Organizer
      第22回基礎有機化学討論会
    • Place of Presentation
      つくば国際会議場(茨城)
    • Year and Date
      2011-09-22
  • [Presentation] Iridium-Catalyzed Regioselective Direct Borylation of Perylene Bisimides2011

    • Author(s)
      Satoru Hiroto, Takuro Teraoka, Satoru Ito, Hiroshi Shinokubo
    • Organizer
      第58回有機金属化学討論会
    • Place of Presentation
      名古屋大学(愛知)
    • Year and Date
      2011-09-06
  • [Book] フォトクロミズムの新展開と光メカニカル機能材料2011

    • Author(s)
      廣戸聡、忍久保洋
    • Total Pages
      159-167
    • Publisher
      シーエムシー出版
  • [Remarks]

    • URL

      http://www.apchem.nagoya-u.ac.jp/hshino/index.html

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Published: 2014-08-29  

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